EP2592107A1 - Copolymères formant des barrières - Google Patents

Copolymères formant des barrières Download PDF

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Publication number
EP2592107A1
EP2592107A1 EP13154420.7A EP13154420A EP2592107A1 EP 2592107 A1 EP2592107 A1 EP 2592107A1 EP 13154420 A EP13154420 A EP 13154420A EP 2592107 A1 EP2592107 A1 EP 2592107A1
Authority
EP
European Patent Office
Prior art keywords
copolymer
fluorinated comonomer
vinylidene fluoride
carbon atoms
vinyl ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP13154420.7A
Other languages
German (de)
English (en)
Inventor
George J. Samuels
George J. SHAFER
Tao Li
Clinton A. Threlfall
Nancy Iwamoto
Eric J. Rainal
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of EP2592107A1 publication Critical patent/EP2592107A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0008—Compositions of the inner liner
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
    • C01B13/02—Preparation of oxygen
    • C01B13/0229—Purification or separation processes
    • C01B13/0248—Physical processing only
    • C01B13/0251—Physical processing only by making use of membranes
    • C01B13/0255—Physical processing only by making use of membranes characterised by the type of membrane
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B5/00—Water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/22—Vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/22—Vinylidene fluoride
    • C08F214/225—Vinylidene fluoride with non-fluorinated comonomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2210/00—Purification or separation of specific gases
    • C01B2210/0043—Impurity removed
    • C01B2210/0062—Water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/16—Homopolymers or copolymers of vinylidene fluoride
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/32—Hydrogen storage
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • Fluorocarbon/Acrylate Coatings are described in U.S. Patent No. 3,716,599 and powder coating are described in U.S. Patent No. 5,030,394 .
  • Solvent based blending is described in U.S. Patent No. 3,324,069 .
  • Polyvinylidene fluoride/polymethyl methacrylate blends are described in U.S. Patent No. 6,362,271 .
  • Other blends are described in U.S. Patent Nos. 5,051,345 ; 5,496,889 (Compatibilized Blends); 4,990,406 (F-terpolymerlacrylate blends). Graft Copolymers are described in U.S. Patent No. 4,308,359 .
  • Polychlorotrifluoroethylene has been employed as a high performance moisture barrier polymer.
  • Comonomers such as vinylidene fluoride, have been introduced to modify water permeation rate or other physical properties ( WO 9306159 and U.S. Published Application No. 2007128393 ).
  • Various fluorocopolymers including copolymers of 2,3,3,3 - tetrafluoro-1-propene and chlorotrifluoroethylene, were disclosed in U.S. Patent No. 2,970,988 as useful in protective coatings and as elastomers.
  • copolymer compositions and the processes for making these compositions according to the present invention are potentially useful commercially.
  • the present invention further provides a process for the preparation of an oxygen barrier copolymer.
  • the process includes the step of contacting in a reaction zone:
  • the present invention further provides a process for the preparation of a moisture barrier copolymer.
  • the process includes the step of contacting in a reaction zone:
  • the copolymer has from about 90 wt% to about 99.9 wt% chlorotrifluoroethylene and from about 10 wt% to about 0.1 wt% of a fluoromonomer.
  • the present invention relates to fluoroolefin copolymers with specific barrier properties and the process for making them.
  • the oxygen barrier copolymer present invention includes from about 50 wt% to about 99.9 wt% vinylidene fluoride and from about 0.1 wt% to about 50 wt% a fluorinated comonomer.
  • the moisture or water vapor barrier copolymer includes from about 0.1 wt% to about 50 wt% vinylidene fluoride and from about 50 wt% to about 99.9 wt% a fluorinated comonomer.
  • fluorinated comonomers and non- fluorinated comonomers may also be used in modest amounts.
  • the diffusivity differences appear to be related to interaction differences of the gases with the polymer composition.
  • the contacting is carried out at a temperature, pressure and length of time sufficient to produce said fluoroolefin copolymer.
  • the initiator examples include azobiscyanoacrylates, aliphatic peresters, such as, t-butyl peroctoate and t-amyl peroctoate, aliphatic peroxides, such as, tert-butyl peroxide, aliphatic hydroperoxides, such as, tert-butyl hydroperoxide, inorganic peroxides such as sodium peroxide, inorganic persulfates such as potassium persulfate, redox initiators involving persulfates as oxidant and sufites such as sodium metabisulfite as reductant, percarbonates such as t-butylperoxide-2-ethylhexylcarbonate, peroxydicarbonates, perhaloacetyl peroxides and a mixture thereof.
  • aliphatic peresters such as, t-butyl peroctoate and t-amyl peroctoate
  • aliphatic peroxides such as,
  • the copolymer of this example was tested for O 2 diffusion. The results are shown in Fig. 1 .
  • the copolymer was also tested for water permeation. The results are shown in Fig. 3 .
  • the general penetration trends for water were opposite that of O 2 and the 1234yf helped to block water.
  • An analogous copolymer having 90 mol% 1234yf and 10 mol% of VDF was prepared in like manner as the above copolymer.
  • the analogous copolymer was tested for O 2 diffusion. The results are shown in Fig. 1 .
  • the analogous copolymer was also tested for water permeation. The results are shown in Fig. 2 .
  • Na 2 HPO 4 /NaH 2 PO 4 buffer 1.34/0.68 g dissolved 180 mL.
  • C 7 F 15 CO 2 (NH 4 ) surfactant 2.44g dissolved with buffer.
  • Add 180 mL of the emulsion solution water/Na 2 HPO 4 /NaH 2 PO 4 / FeSO 4 / C 7 F 15 CO 2 (NH 4 )).
  • Example 3 Chlorotrifluoroethylenel1234yf Copolymer and Moisture Permeation Comparison with other Chlorotrifluoroethylene Polymers
  • the CTFE/1234yf copolymer was formed into a film of 1.00 mil thickness by using a film gauge and a heated carver press.
  • the CTFE/1234yf copolymer was tested for moisture permeation against a CTFE homopolymer and two CTFE/vinylidene difluoride (VF) copolymers (3 wt% and 5 wt% vinylidene fluoride).
  • the films of the CTFE homopolymer and two CTFE/vinylidene difluoride (VF) copolymers were prepared in substantially the same manner as for the CTFE/1234yf copolymer. Films were typically of 50cm 2 area and 1.00 mil thick. A MOCON Water vapor permeation system was used for the measurements.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
EP13154420.7A 2006-12-20 2007-12-20 Copolymères formant des barrières Withdrawn EP2592107A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US87100606P 2006-12-20 2006-12-20
EP20070869658 EP2094604A4 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP07869658.0 Division 2007-12-20

Publications (1)

Publication Number Publication Date
EP2592107A1 true EP2592107A1 (fr) 2013-05-15

Family

ID=39562935

Family Applications (3)

Application Number Title Priority Date Filing Date
EP20070869658 Withdrawn EP2094604A4 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières
EP13154423.1A Withdrawn EP2592108A1 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières
EP13154420.7A Withdrawn EP2592107A1 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières

Family Applications Before (2)

Application Number Title Priority Date Filing Date
EP20070869658 Withdrawn EP2094604A4 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières
EP13154423.1A Withdrawn EP2592108A1 (fr) 2006-12-20 2007-12-20 Copolymères formant des barrières

Country Status (5)

Country Link
US (2) US8163858B2 (fr)
EP (3) EP2094604A4 (fr)
JP (2) JP5167272B2 (fr)
CN (2) CN103396506A (fr)
WO (1) WO2008079986A1 (fr)

Families Citing this family (34)

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EP2297214B1 (fr) * 2008-07-07 2012-09-19 Arkema Inc. Copolymères de fluorure de vinylidène/2,3,3,3-tétrafluoropropène
CN102177118A (zh) * 2008-10-10 2011-09-07 纳幕尔杜邦公司 包含2,3,3,3-四氟丙烯、2-氯-2,3,3,3-四氟丙醇、乙酸2-氯-2,3,3,3-四氟丙酯或(2-氯-2,3,3,3-四氟丙氧基)氯化锌的组合物
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US9321867B2 (en) * 2012-12-21 2016-04-26 Honeywell International Inc. Synthesis of 2,3,3,3-tetrafluoropropene/vinylidene fluoride copolymers
FR3004185B1 (fr) * 2013-04-03 2017-10-13 Arkema France Terpolymeres contenant du fluorure de vinylidene et du trifluoroethylene
US9782730B2 (en) * 2013-05-14 2017-10-10 Honeywell International Inc. 1234YF- and 1234ZE-based polymeric membrane materials, membrane preparations and uses thereof
US9394394B2 (en) 2013-09-30 2016-07-19 Honeywell International Inc. Synthesis of chlorotrifluoroethylene-based block copolymers by iodine transfer polymerization
US10435580B2 (en) 2015-11-20 2019-10-08 Honeywell International Inc. Gloss retentive fluorocopolymers for coating applications
JP6702864B2 (ja) * 2013-10-22 2020-06-03 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． テトラフルオロプロペンから形成される硬化性フッ素ポリマー
EP3230329A1 (fr) * 2014-12-09 2017-10-18 The Chemours Company FC, LLC Copolymères de 1,3,3,3-tétrafluoropropène
CN108351278A (zh) 2015-06-05 2018-07-31 威廉·T·韦切雷 低渗透率样品袋
US20190002656A1 (en) * 2015-08-26 2019-01-03 Bemis Company, Inc. Anti-Scalping Pharmaceutical Packaging Film
US11015005B2 (en) 2015-11-20 2021-05-25 Honeywell International Inc. Fluorocopolymers for coating applications
EP3377586A4 (fr) * 2015-11-20 2019-10-16 Honeywell International Inc. Fluorocopolymères de rétention de brillant pour applications de revêtement
US20170165613A1 (en) * 2015-12-09 2017-06-15 Honeywell International Inc. Hollow fiber membranes formed from trans-1,3,3,3-tetrafluoropropene and vinylidene difluoride fluoropolymers
EP3453054A4 (fr) * 2016-05-03 2020-01-01 Honeywell International Inc. Dispositifs et composants électroluminescents dotés d'une résistance chimique améliorée et procédés apparentés
JP2019521505A (ja) * 2016-05-03 2019-07-25 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． 改善された化学物質性を有する発光装置及び構成要素並びに関連する方法
US10294340B2 (en) 2016-07-27 2019-05-21 Honeywell International Inc. Film layers and methods for forming the same
CN111564516A (zh) * 2020-05-20 2020-08-21 浙江晶科能源有限公司 一种降低湿热衰减的阻隔型光伏焊带
WO2022124253A1 (fr) * 2020-12-07 2022-06-16 ダイキン工業株式会社 Copolymère ainsi que procédé de fabrication celui-ci, agent de liaison, et article moulé

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